


Day 3 - First time

by WorkInProgress84



Series: NSFW Challenge [3]
Category: Check Please! (Webcomic)
Genre: Age Difference, First Time, M/M, PWP, Rimming
Language: English
Status: Completed
Published: 2019-04-30
Updated: 2019-04-30
Packaged: 2020-02-10 11:13:07
Rating: Explicit
Warnings: No Archive Warnings Apply, Underage
Chapters: 1
Words: 3,591
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/18659299
Author URL: https://archiveofourown.org/users/WorkInProgress84/pseuds/WorkInProgress84
Summary: Jack sneaks out of his hotel room after a disastrous game and ends up in a bar, meeting a not-so-incognito hockey player. They both like what they see.





	Day 3 - First time

**Author's Note:**

> I imagined Jack to be much younger than Kent in this one (don't ask me why it went there, I have no idea) but I left it vague enough on purpose.

«Want to take this somewhere more private ? » Kent panted into Jack’s ear, his wandering hand already skimming across Jack’s ribs underneath his shirt.

Jack was out of breath, too: Kent’s mouth was… something else. It was the smirk that had drawn him in first when he’d spotted the blonde at the bar, nursing what looked like whiskey with a forlorn expression on his face. Of course he'd recognised him. Of course he'd pretended he hadn't: Jack figured the guy hadn't chosen this dump of a bar by accident.

The smirk had transformed Kent’s face completely when he’d caught Jack staring from his booth. Jack had looked down; after all, he wasn’t supposed to be here. He wasn’t 21 yet and he was taking a considerable risk by breaking curfew. He’d also desperately needed to get out of his head, and if it meant using his brawn to his advantage for once, so be it.

The briefest of introductions had barely been made (Kent had given his real name) when Jack had found himself pressed up against the wall in the shadowy alley by the bar, Kent’s tongue plundering his mouth, his hard dick grinding into Jack’s with purpose, hands roaming everywhere. Kent’s whispers of “so good, so damn pretty” an oh-so-flattering balm murmured against Jack’s skin.

“Yeah, let’s go,” Jack nodded, his dark hair falling into his face.

Kent flashed him a predatory smile that had Jack trembling with arousal. He knew what was going to happen, counted on it, even; it didn’t mean there wasn’t some trepidation there. Kent pressed a filthy kiss to his mouth, a promise of wicked things to come, then took his hand and tugged him down the street to his car, the kind that screamed its owner was overcompensating, except he’d felt all of Kent and it definitely wasn't the case here.

The ride was mostly silent, thick with anticipation. Kent’s right hand inched ever closer to where Jack craved to feel it the most, kneading the flesh until Jack thought he would burst with frustration. He was out of his mind with lust by the time they reached Kent’s apartment and he would have been hard-pressed to say what part of town they were in. Fleetingly, he wondered how dangerous this situation he’d thrown himself into was; Kent was famous, okay. It didn't mean he couldn't be a psychopath who intended to stuff his disassembled body parts in his freezer, and no one would ever find him because Jack hadn’t told anyone he was going to sneak out of his hotel room. So that was something he should have considered. On the other hand, Kent had latched onto the side of his throat and started sucking a bruise there when they’d stopped at a red light, so who cared about dying anyway, surely this was the best way to go.

“God, I am going to ruin you, you gorgeous creature.” Jack couldn’t help but let out an embarrassed laugh at the cheesy line, although Kent smothered it pretty quick when he palmed his rock-hard dick through his jeans. “Mmh, that’s more like it.” He licked a long, slow line up Jack’s throat before he bit on his earlobe, making Jack groan and buck into Kent’s hand. “Exactly.”

Kent dragged Jack through his house until they stumbled through his bedroom door and onto his bed, leaving a trail of clothes in their wake, and when Kent finally settled on top of him, strong thighs on each side of him, Jack let his hands explore with wanton abandon; he’d never seen, much less touched someone as beautiful as Kent with his light blue eyes – now no more than a ring of colour around his dilated pupils, and all his soft skin over lean muscle. Kent let him explore to his heart’s content, a smug little grin tugging at the corner of his mouth. God, his mouth was indecent, and Jack was struck with the need to feel it around his cock, hips hitching up again.

“Did you want something?” Kent said with the rise of an eyebrow and a smirk that was as infuriating as it was sexy. Jack wanted nothing more than to see this man choke on his dick.

“I want you to suck me off,” Jack breathed, making himself blush with his own boldness.

“Mmh, my pleasure.”

Kent bent over to steal another kiss from Jack, demonstrating exactly what he was capable of, plunging in then retreating, all drugging sweeps of tongue and dragging lips, a hint of teeth to keep things interesting, and then he was moving down, nipping at Jack’s skin, pinching his nipples lightly; Jack cried out.

“We’ll definitely need to revisit this for round two,” Kent promised darkly just before he sucked the head of Jack’s cock into his mouth.

Jack gasped and his eyes rolled to the back of his head as his hand went to fist Kent’s hair. None of the girls who’d done that for him had felt like this. The front of Kent’s teeth rubbed against the spongy head of him, short-circuiting his brain, and then Kent’s tongue darted out, just far enough to tease at the slit. Jack felt a glob of precome shoot up his dick, slicking Kent’s lips like some kind of obscene lipgloss. Kent looked up through long, blonde eyelashes - so that was what people meant when they talked about eye-fucking – and then he slowly sank down slow on Jack’s dick, his gaze never leaving Jack’s. Jack could have sworn he moaned the entire time it took Kent to take him to the root, the head of his cock snug at the back of Kent’s throat.

“Don’t stop,” he choked out, his hand tightening in Kent’s hair. Kent just groaned, sending beautiful vibrations that reverberated through Jack’s entire body, wrenching another pitiful moan from his throat.

Kent didn’t stop; he came back up only to swallow all of Jack down all over again, up down, up down, until the motion made him dizzy and he felt like he would pass out from so much pleasure. Jack tried hard to stay still for Kent but he couldn’t always, not when the hands that were holding him down strayed down to tug lightly on his balls; Kent didn’t seem to mind, only opened his mouth wider to let Jack fuck into it once, twice. He shamefully realized he was on the verge of crying, the pleasure so overwhelming he couldn’t stand it.

Maybe Kent saw him, maybe his jaw was sore from doing so many wonderful things to Jack’s dick, but he pulled off. Jack was embarrassingly out of breath already, but at least he hadn't come, and his sorry state was also a testament to Kent’s sexual prowess so it couldn’t be that bad. Hopefully it didn’t scream “virgin” too loud; the very thought made him cringe.

Jack was already psyching himself for the main event, a touch nervous, when Kent guided his legs up and outwards like Jack was some kind of gymnast. He was lucky Jack considered flexibility an advantage in the game and he could easily accommodate the awkward position, although Kent was looking at him like he was a spread at a feast and that sure was gratifying. 

Kent leaned down again, kissing and giving his cock little kitten licks before he carried on downwards to lavish attention on Jack’s balls, gently taking them in his warm mouth and rolling them on his amazing tongue. Jack tried holding onto the sheets to ground himself and keep from writhing, but he couldn’t help the punched out sound when Kent released his balls to slide on down and lap, just once, at the skin beneath. His cock leaked an embarrassing amount of precome on his stomach. 

“No one’s ever done this for you?” Kent asked with a cocky grin. The touch had effectively robbed Jack of his power of speech so he settled for shaking his head. “What a shame. Mind if I keep going?” He nodded with so much force that his fringe flopped into his eyes. Kent laughed. “Hold yourself open for me - yeah, just like that, you’re magnificent.”

He bent back over Jack and spread his cheeks, dipping low to blow cool air on Jack's rim. He gasped and clenched around nothing. Kent brushed his lips across Jack’s hole; his entire body spasmed, so Kent did it once more before he started circling the tight nub. Only when Jack was starting to get used to this new sensation did Kent lick another narrow stripe up his taint; it was like someone had punched the breath out of him. Kent _looked_ at him and then went to town, diving in like a parched man at a well, slobbering all over him, the obscene sounds of Kent's ministrations driving Jack as crazy as the actual sensations on his flesh; Kent spread him even further and devoured him with delighted frenzy: he licked and nibbled, sucked and kissed, alternating between firm strokes and feather-light jabs until Jack was out of his mind with lust and so relaxed Kent had no problem dipping the tip of a thumb in his ass.

When Kent’s digit breached him, Jack lost his breath all over again and a thick glob of precome dribbled down his stomach. Kent pressed a reassuring kiss to his inner thigh and started flicking his tongue all around his finger, relentlessly pressing inside and stretching him further. He kept at it for what felt like blissful, torturous hours, until Jack was relaxed again, shooting stars exploding behind his eyelids, and then pushed in his second thumb by the first. Jack whimpered once and then felt like he couldn’t stop the entire time Kent worked him open, whispering encouragements against his hole until Jack was just loose enough for him to dart his tongue inside. Jack cried out, dignity be damned, and wrapped a punishing hand around his cock to keep from coming on the spot.

Kent finally let him go and smirked at him, looking for all intents and purposes like the cat that got the cream. If this was Jack's reaction to mere foreplay, he was afraid there would be no concealing his newness to the whole business once Kent actually got his dick in him... God, he couldn’t wait for it.

“You alright there, sweetheart?” Kent asked as he trailed a chain of kisses up the sensitive skin of his groin. He didn’t look too alarmed by Jack’s reaction. 

“Yeah, it's just- that was… Um, keep going?”

“Of course.”

While Kent went off to rummage in his bedroom, Jack remained on the bed, feeling like his whole body was liquid. He probably should’ve been paying more attention, the guy could still turn out to be a serial killer, could still be digging up his most trusted saw to slice Jack into Canadian cutlets, but for now Jack’s very soul was singing and it was exactly what he’d been after when he’d entered that bar.

He became aware of Kent again when he scooted between his legs. Jack automatically lifted them again for easier access and Kent grinned at him.

“You want me to fuck you like this?” he asked even as he stuffed a pillow under Jack’s lower back for easier access.

“Yes, please.”

“Good boy.” A pleasant thrill went through Jack; Kent’s gaze turned shrewd. “That’s good to know.”

Jack felt like he’d just given himself away, but he lost track of why that could be a bad thing when Kent inserted a lubed-up finger, then quickly another, in him. It was uncomfortable at first, but complaining was out of the question: the end goal was literally in sight, Kent’s glorious cock fat and long and he wanted it like he’d never wanted anything before. 

Jack indulged and reached down to stroke it, his first proper feel of another man’s cock, and marvelled at how different and yet how similar it was to his own as it jerked in his hand and Kent gave a very gratifying groan. He could see how some people became addicted to this; Jack could absolutely see himself work to satisfy his partner exactly the way he needed. 

When he hissed at the third finger, Kent gently shushed him and slowed things down a little. He wasn’t a serial killer, Jack decided: he couldn’t imagine serial killers as considerate lovers, and Kent was proving to be just that - relentless, yes, but considerate. Jack leisurely tugged on his cock, his arousal having abated a little with the discomfort of being stretched so thoroughly.

“Are you good to go?” Kent asked through gritted teeth. Jack’s wandering hand on his dick probably wasn’t helping, but it was payback for torturing him with his tongue and his fingers earlier.

“I think we should just test it. Put your cock in me,” he said coyly, biting his lower lip and trying to make it as seductive as he could. He wasn’t a dirty talk kind of guy, but with Kent it felt like he should be.

“Look at you, so eager to please.” A shiver went down Jack’s spine. 

And then Kent was removing Jack’s hand from his dick to put on a condom and lining up along the fingers that were already in Jack’s ass. The second he pulled them out he started pushing in. Jack’s hole put up a valiant effort to resist the invasion even though Jack tried to relax like the internet had told him to but the internet had _lied_ , it _hurt_.

Kent stopped once the head of his cock had popped in. A fine sheen of sweat covered Jack’s body as he panted openly and blinked in hopes of making the black spots that danced before him go away. And, just great, his erection had flagged again. Now Kent was going to think he wasn't enjoying this. He _was_ , but it _hurt_.

“Jack.” He stubbornly refused to make eye contact. “ _Jack_ ,” Kent insisted. Jack knew he was so busted. “Have you done this before? Is it your first time?”

“It’s not my first time.”

“With a man,” he added, slightly breathless from holding still inside Jack.

“Oh. Um.” He considered lying, but then he also considered how uncomfortable he was right then. “Yes-but-please-don’t-stop.”

Kent cursed. “I’m not going to stop if you don’t want me to,” he huffed. Jack sighed in relief. “But if you’d told me, it would’ve made things easier, you know?” Jock nodded, a bit sheepish. “I would have had you on all fours, for starters… You sure you’re good like this?” he asked with the lightest hitch of his hips, making Jack gasp.

“Yes. Please.”

“Canadians. Always so polite,” Kent chuckled as he recoated his cock with more lube and started pushing forward.

“Fuck you,” Jack gasped, but the heat of it was lost as Kent sank into him, oh-so-slowly but inexorably filling him up. It felt like ages until he was seated to the hilt, the burn so intense Jack felt like he was going to burst. Kent slowly stroking his cheek brought him back to the here-and-now, a soft, welcome counterpoint to the feeling between his legs; Kent felt immense in him.

"Breathe through it, gorgeous. Just breathe. Or I can pull out." Jack shook his head. “Didn’t think so.”

Kent resumed kissing him, the minuscule movement as he bent down ripping a whine out of him that Kent soothed with his lips and with the hand that he sneaked between them to stroke him back to arousal. 

"God, you're so hot and tight around me, gripping me like a vise, _Jack_. Do you know how hard it is not to just take you right now? Take what I want from you? You look incredible, all flushed and needy." Kent ran an insistent fingertip over his slit and Jack whimpered. "Yeah, you want my cock, don't you? You're gagging for it, sweetheart, so amazing."

The cajoling words worked wonders on Jack's erection, and before he was aware of doing it, his hips started hitching up, seeking the long-awaited friction. He fucked himself on Kent's cock, shallowly, mimicking the movements of Kent's tongue in his mouth.

"Can you- Can we-?" Jack stuttered, not sure how to ask for what he craved.

"God, yes," Kent hissed as he went back to his knees to pull out. Jack felt oddly gratified to know he wasn’t the only one who wanted it this bad.

Jack gasped at the great, slow drag of Kent's cock in him, the easing pressure a temporary reprieve before Kent pushed back in, spreading more lube on his cock. It didn't feel any less of an invasion the second time or the third or the fourth, and Jack couldn't smother the broken moans coming from his mouth, but Kent didn't seem to mind, taking his cues from them instead, adjusting angles and rhythm after Jack’s reactions.

The burn eased after a while and Kent obviously could tell because his thrusts reached deeper, their intensity growing until Jack cried out at a particularly well-aimed one against that sweet spot inside him that had him seeing stars. Obviously nobody had ever touched it before, and Jack felt like crying from how divine it felt. The knowing grin Kent flashed him as he aimed for it again and again tore a great laugh out of Jack even as he struggled to breathe through Kent’s relentless pounding. His moaning got so loud he hoped Kent’s neighbours were elderly or deaf or non-existent because there was no way he could stop himself.

Kent’s laser-like focus was a true joy, how ruthless he was in his ministrations, engineering Jack’s pleasure like he was his pet project. Kent held onto his thighs strongly enough to leave finger-shaped bruises, which meant Jack would have to be careful around the locker room for a week, but every one of those bruises would be worth it for the way they made him feel cherished and owned right now. Jack did a bit of owning of his own, letting his palms run along the muscled planes of Kent's chest like he had every right to. Everything about him was perfect (the first man he’d ever touched and what a outstanding choice), from the dusty pink of his pebbled nipples to the slight curve of his hips; he couldn't believe how gorgeous he was.

Jack realized his own dick was crying for attention when a particularly forceful thrust bumped it against his own stomach. He’d leaked so much precome all over himself already, he didn't even need lube to slick himself up. He palmed it and started stroking, but the pleasure remained secondary to that of being split open on Kent's cock and so thoroughly claimed. 

“God, you look so fucking good like this,” Kent growled as he drove into him with enough force to jostle him up the bed. "You look so high you can barely keep your eyes open, you wanted it so bad. Do you like my cock in you? Do you like it, Jack? I bet you love it. I think you were made to have a cock in you, keeping you happy. I can't wait until you're sucking on mine, your mouth is gorgeous I bet you're a natural, you'll just swallow me down like the champion you are, swallow every last drop until you've sucked me dry. You'll swallow all of me, won't you, Jack?"

Jack looked at Kent through hooded eyes, which was indeed the best he could do, so completely entranced was he with Kent's filthy monologue and the feeling radiating from his hole. The pressure had been building for so long, and the combination of pistoning hips and obscenities was so amazing, Jack surrendered to his orgasm completely, every nerve ending in his body singing with ecstasy as his cock pulsed in his hand, painting his stomach with thick white ropes. It slammed into him so strongly, he couldn't believe he'd barely touched himself to get here. 

Still Kent's thrusts went on as he chased his own climax; it didn't take more than a handful for him to bury himself as deep as he could go and spill inside Jack, feeling every twitch of this great cock. Jack felt like his own orgasm wouldn't quit; intellectually, he knew those were probably only aftershocks, but aftershocks had never felt quite like this before.

When he became aware of his surroundings again, he realized he'd been chanting his reply to Kent's question the whole time he'd been coming, the breathless yesses rolling off his tongue like forever promises. Kent plopped down on his chest, not paying any attention to the mess on his stomach, and sealed his mouth over his, sloppy and sated, and even though Jack was quite sure he was spent (at least until he took a power nap), he grabbed at Kent's hair to pull him in closer, still full of passion for this man.

"Stay?" Kent asked quietly, slowly pulling out so as not to hurt him.

"Yes," Jack replied through a whine. "I believe I have a cock to suck dry." 

Kent groaned. "First, nap. Then, bath. Then we can start on Advanced Cocksucking since you seem to be quite the fast learner, Wonder Boy."

"Yes, sir."

If Jack didn't mistake the heated look Kent threw his way, it looked like he was onto something himself, and he couldn't wait to explore it further. In these matters at least, luck seemed to favor the bold.


End file.
